Piers-Rubinsztajn (P-R) conditions, involving catalysis by tris(pentafluorophenyl)borane, were applied to siliconize triarylamines. A phenylated linear methylhydrosiloxane copolymer was utilized to create a hydrolytically-stable composite with promising optical, electrochemical and thermal properties. However, the reaction was highly exothermic, had rapid uncontrollable kinetics and produced methane as a byproduct; problematic characteristics for larger scale syntheses. Thereafter, triarylamines with bulkier substituents were studied to determine whether the kinetics could be slowed and a less volatile byproduct created. The rate of conversion was retarded significantly as expected, but not all derivatives reacted quantitatively in ambient conditions. Finally, P-R conditions were applied to methylhydrosiloxane-dimethylsiloxane copolymers. Gelation in air upon extended reaction time was effectively avoided by “finishing” excess Si-H sites using anisole. The result was the preparation of composites with up to 61 wt % arylamine content, which are expected to have significant applications as cost-effective flexible hole transport layers in organic electronic devices.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/33226 |
| Date | 20 November 2012 |
| Creators | Gretton, Michael James |
| Contributors | Bender, Timothy |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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